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by Novachester



Category: Supernatural
Genre: Dean in Makeup, Dean in Panties, F/M, Feminization, Genderfluid Character, Genderfluid Dean, M/M, consensual sexual situations
Language: English
Status: Completed
Published: 2014-05-01
Updated: 2014-05-01
Packaged: 2018-01-21 13:22:27
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,620
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1551968
Author URL: https://archiveofourown.org/users/Novachester/pseuds/Novachester
Summary: <blockquote class="userstuff">
              <p>Dean has always felt a sense of displacement, and it takes a long time to figure out why.</p>
            </blockquote>





	Home

Dean’s three years old the first time Mary catches him playing with her things; making a mess of her powder and struggling to twist open her lipstick. He’s petrified that she’ll be angry, that despite trying his best to be tidy, he’s ruined all her pretty things. Instead, she takes a deep breath and smiles at him, gentle, if not a little strained.  
  
“Sweetheart, please don’t play with mommy’s makeup,” she says, easing the lipstick from his hands. “They’re not toys.”  
  
“I know,” Dean says quickly, leaning timidly against her as she wraps her arms around him, leaning over him as she tidies up the vanity. “I wanted to have red lips too, like you. I’m not bad,” he says, tears welling rapidly in his eyes. He’s watched her do it hundreds of times, and she always looks so beautiful after, like the women Dean sees on TV or in magazines. His mommy is _perfect_.  
  
Mary stops tidying so that she can look down at her boy, a soft, sympathetic laugh escaping her. “Oh, baby,” she coos, scooping him up into her arms so she can sit at the vanity, adjusting him in her lap. “No, baby, you’re not bad at all. Here, let me show you.”  
  
They spend an hour like that, Mary carefully applying Dean’s lipstick, a little blush and even some eye shadow. Dean can’t stop laughing, thrilled by the shift in his appearance, but the game comes to an abrupt halt when John comes home.  
  
John and Mary fight. They shout again and again, and even from his bedroom, Dean hears every word of it. He doesn’t know why it made his daddy so mad, but he knows it’s his fault. He runs to the bathroom and scrubs off every bit of the makeup, rubbing his skin raw on the towels. He never touches his mother’s makeup again, despite her gentle encouragements.  
  
A year afterwards, he regrets every single instance in which he declined playing makeup with his mom.  
  
  
Fast-forward sixteen years later. Dean spends just about every bit of free time he has picking up dates, meeting people in bars he shouldn’t legally be in. He’s scoping out the bar when a woman approaches him, dark skin, a sly smile and legs that go on forever. She introduces herself as Rhonda and asks if she can buy him a drink. Barely an hour later, Dean’s in her apartment and she’s straddling him atop her bed.  
  
“Do you want to try them on?” She asks, tracing her fingers along Dean’s chest.  
  
Dean’s head nearly spins off his neck at the speed with which he turns, looking at her with wide, confused eyes. “What?”  
  
“The panties,” Rhonda clarifies, an amused little smile playing on her lips. “You’ve been staring at them for a while… It’s okay if you do. I think you’d look good,” she tells him, reaching up to grab the pink panties hanging off her bedpost. She stretches them between her hands, staring down at Dean, his cheeks flushed dark red, full lips parted uncertainly. “It’s okay, sweet boy. Let’s have some fun.”  
  
Not only does Rhonda let him wear her panties, she curls her dainty fingers around his jaw and holds him steady while she carefully applies a sheer red to his lips, murmuring compliments every step of the way, admiring the curl of his lashes and the natural pout of his mouth. She muses what he might look like with pretty long hair, and he admits to having wondered the same.  
  
She doesn’t say anything when he starts to cry. He leans into her and she holds him, runs her fingers through her hair and soothes him through it. She tells him over and over that it’s okay, it’s okay, _it’s okay, and it always was_.  
  
They don’t sleep together that night, but they meet again twice more where they do. When Dean reluctantly tells her that he’s leaving town, she kisses his forehead and hands him a compact and a tube of lipstick.  
  
 _It’s okay. It always was._  
  
Four years later, Dean’s still not exactly sure what to call this feeling, other than _weird_. The word sticks to him a horrible brand, hot on his skin and damn persistent, but there are echoes of kind voices and gentle hands that are occasionally strong enough to override it, that let Dean indulge and be the part of himself he doesn’t always feel safe being.  
  
Sam leaves for Stanford and Dean’s sure it’s his fault.  Nothing about their lives has ever been _normal_ , but leave it to Dean to make matters worse. Did Sam find his tiny stash of underwear, or the makeup he keeps in a plastic bag at the very bottom of his duffle?  
  
He doesn’t know, and it doesn’t seem like he’ll ever find out. Sam isn’t answering, and eventually, Dean stops calling.  
  
With his dad around less and less, Dean starts to feel a little safer to indulge just a touch more. He drives two towns over from where he’s staying to find a sketchy enough sex shop that he can dip into, buy lingerie and not receive so much as a second glance.  
  
Staring in the mirror, Dean is breathless. Maybe it should feel a little ridiculous, the tiny length of the skirt and the ill-fitted blouse, but fuck, Dean _loves_ it. He loves the feel of the stockings on his legs, the pressure of the garter straps along his thighs, all of it. It feels _right_ , and Dean doesn’t know how to reconcile the wave of relief with the nausea of wondering what his dad would say if he could see him now.  
  
 _I’m not bad,_ Dean thinks, shakily covering his face, struggling to take a deep breath. _I’m not bad._  
  
Clear as a bell, he hears his mother’s voice respond, _No, baby, you’re not bad at all.  
  
_ Dean starts taking more chances, seeking different kinds of partners. He’s always felt the eyes of men on him at bars, and maybe in high school he messed around in the locker rooms with inexperienced hand jobs and awkward grinding sessions, and maybe he knows what it feels like to have fingers slip inside him, but Dean wants something _more_. He wants big hands on his hips, stubble burn on his thighs; he wants to feel small in the hands of someone larger.  
  
It doesn’t take Dean long to find what he’s looking for. The guy is big, but not someone Dean couldn’t handle if things went south. He’s got kind brown eyes and a wide, handsome smile, made even more charming by the slight gap between his front teeth.  
  
His name is Mark and he works in a boutique downtown selling women’s shoes. He’s got a nice enough apartment, the kind where you use coasters on the coffee table and take your shoes off in the hall. Mark doesn’t seem to care about that right now though, too busy shoving his hands under Dean’s clothes, kissing at the crook of his neck.  
  
Dean’s both breathless and shirtless by the time they get to the bedroom, where Dean drops unceremoniously onto the bed, eyes wide, cock straining in his jeans. He’s had some dominant women before, but none of them were able to handle him like this. None of them managed to make him feel delicate like this.

When Mark yanks Dean’s jeans down, it’s the first time another man has seen him like this. The panties are purple, a color he’s always known would look nice with his eyes, and the front of them are soaked through with precome.Mark looks like he’s had the air punched out of him, and for a split second, Dean’s terrified.  
  
When their eyes meet, Mark breathlessly asks, “You that wet for me, baby?”  
  
Dean’s cock jerks and he nods. “Soaked.”  
  
Mark holds Dean down and fucks him hard, but Dean only comes when Mark leans in and murmurs _That’s it, that’s good, doing so good, baby girl._  
 __  
  
After that night, Dean starts experimenting with gender pronouns.  He chooses a day, and decides that for the entirety of that particular day, he’s going to internally refer to himself as ‘she.’  
  
Dean starts the morning of that day by brushing her teeth, washing her face in the dingy motel bathroom and applying a powder foundation. She winds up not thinking very much of it, though, deciding it makes her freckles look too dusty, but she likes the way it mattes out the usual shine her skin has. She uses a taupe eye shadow and lines her eyes with a dark grey liner, a trick she’d learned from a magazine once. The green of her eyes pops so much, looks so vibrant; it makes her look alive.  
  
 For her lips, she uses a sheer red, careful not to go beyond her natural lip line. She contemplates plucking her eyebrows, but that would be too lasting, too noticeable. She has to brush the thought away quickly, not linger anywhere too dark, and remind herself that today belongs to _her_.  
  
She’s gotten her hands on better fitting clothing since that terrible sex costume she’d first picked up.  After a few thrift store trips, she managed to pick up a nice high waist A-line green skirt and a white blouse to match it, neatly tucked into the skirt. It looks like something Mary might have worn, and as Dean looks at her reflection in the mirror, she realizes just how alike she and her mother look. Full red lips, softly lined eyes and light pink cheeks.  
  
Dean sees in herself the beauty she always saw in her mother, but more than that, she feels it. She feels _home_.

**Author's Note:**

> commissioned on tumblr! if you're interested in commissioning me, message me here or check out my tumblr! novachester.tumblr.com/tagged/commissions


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